N,N-Dimethylethylenediamine → HCID 68865837, compound

HRID 1725940Notes

Reaction equation

HRID 1725940 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH:16]=[C:15]([CH3:22])[C:14]=2[C:13]=1[C:23]([O:25]C)=[O:24])(=[O:10])=[O:9].[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30][NH2:31]>C(#N)C.C(N(CC)CC)C>[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30][NH:31][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH:16]=[C:15]([CH3:22])[C:14]=2[C:13]=1[C:23]([OH:25])=[O:24])(=[O:9])=[O:10]

Participants

5

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 68866398HCID 68866398, compound

Product 1

HCID 68865837HCID 68865837, compoundYield 103.3%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of Example 275E (50 mg, 0.133 mmol), N,N-dimethylethylenediamine (117 μl, 1.06 mmol), and triethylamine (56 mL, 0.4 μmol) in 0.5 mL of acetonitrile was heated to 200° C. for 1200 seconds in a microwave oven. The obtained reaction mixture containing a crude product was purified by reverse phase column chromatography to provide 59 mg of the desired product. MS (ESI(+)) m/e 430 (M+H)+; MS (ESI(−)) m/e 428 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 7.48 (dd, 1H), 7.42 (d, 1H), 7.06 (d, 1H), 6.93 (d, 1H), 6.66-6.76 (m, 2H), 6.10 (t, 1H), 5.99 (t, 1H), 5.75 (s, 3H), 3.59-3.64 (m, 2H), 3.25-3.30 (m, 2H), 2.85 (m, 6H), 2.54-2.56 (m, 2H), 1.96-2.09 (m, 5H).

Workup

  1. customThe obtained reaction mixture
  2. customwas purified by reverse phase column chromatography

Sources & evidence

ORD record
ord-05192e5b48974fd5abca6443887d4042
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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